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Mutagenicity of quinones: pathways of metabolic activation and detoxification.
Open accessAbstract
The mutagenicity of various quinones, a class of compounds widely distributed in nature, is demonstrated in the Salmonella TA104 tester strain. The metabolic pathways by which four quinones, menadione, benzo[a]pyrene 3,6-quinone, 9,10-phenanthrenequinone, and danthron, caused mutagenicity in this test system were investigated in detail as were the detoxification pathways. The two-electron reduction of these quinones by NAD(P)H-quinone oxidoreductase (DT-diaphorase) was not mutagenic, whereas the one-electron reduction, catalyzed by NADPH-cytochrome P-450 reductase, was mutagenic, except for danthron, which was only slightly mutagenic. The mutagenicity of the quinones via this pathway was found to be attributable to the generation of oxygen radicals. The cytochrome P-450 monooxygenase also played a significant role in the detoxification and bioactivation of these quinones. For example, phenanthrenequinone was converted to a nonmutagenic metabolite in a cytochrome P-450-dependent reaction, whereas danthron was converted to a highly mutagenic metabolite. These studies show the complexity of metabolic pathways involved in the mutagenicity of quinones.
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Cites
Cadenas, E., Boveris, A., Ragan, C. I., & Stoppani, A. O. M. (1977) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(77)90035-2 · Cited by 855
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Transcriptional regulation of the rat NAD(P)H:quinone reductase gene
Favreau, L. V., & Pickett, C. B. (1991) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(20)64358-7 · Cited by 497
The diverse functionality of NQO1 and its roles in redox control
Ross, D., & Siegel, D. (2021) · Redox Biology · doi:10.1016/j.redox.2021.101950 · Cited by 499
Metadata
- Authors
- Chesis, P. L., Levin, D. E., Smith, M. T., Ernster, L., & Ames, B. N.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 1984-03
- Volume
- 81
- Issue
- 6
- Pages
- 1696-1700
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2094779562
- Cited by
- 388
- References
- 1
- FWCI
- 26.92
- Type
- journal article
- Language
- en
- Open access
- green
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- Chesis, P. L., Levin, D. E., Smith, M. T., Ernster, L., & Ames, B. N. (1984). Mutagenicity of quinones: pathways of metabolic activation and detoxification. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.81.6.1696
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